870. - Tom Freston

14 Nov 2025 · 1 h 12 min · 31 chapters

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In short

Episode topic: Tom Freston (former MTV/TV executive) discusses his post-cable career, promoting a book, poverty advocacy via the One Campaign, and his long relationship with Afghanistan and media/education there; he also reflects on how MTV and cable-era entertainment changed after the digital revolution.

Guest backgrounds

Tom Freston is a Manhattan-based media executive turned philanthropist/advocate; he’s board chair of the One Campaign (stand-by poverty advocacy focused on Africa) for 18 years. Hosts are How Long Gone’s Jason and Chris, who trade NYC/LA anecdotes and discuss entertainment, health, and media culture.

Key claims

Freston says cable’s “cash machine” era (80s/90s) ended as internet/social media fragmented audiences; he left around 2006. He argues Nielsen-style measurement is less accurate now due to infinite fragmentation, while podcasts are easier to track. He claims entertainment creativity suffered as consolidation reduced “outsized characters” and risk-taking.

Notable examples

Afghanistan work includes helping set up the first commercial TV after the Taliban, later shifting to educational programming for marginalized Afghan women funded by foundations (Malala/Gates). He describes hitchhiking overland on the Silk Road in 1972, praising hospitality and recounting being offered “world’s finest” hashish at immigration. He recalls MTV’s news operation and how MTV later became dominated by reality shows.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Podcasting Setup Challenges

0:45 to 2:00

Discussion about podcasting equipment issues due to an event.

Writer's Room Culture

2:00 to 5:00

Hosts share humorous anecdotes about writer's room snacks and culture.

“Look, you put your cheeses in front of me, it's going to be tough.”

Concert Experiences and Mask Culture

5:00 to 8:00

Insights on concert atmospheres and mask usage post-pandemic.

Dining and Food Discussions

8:00 to 9:30

Hosts discuss various restaurants and food experiences in New York.

“He's wearing the hat, so it was a giveaway, but good restaurant.”

Creative Collaboration Ideas

9:30 to 12:29

Exploration of the idea of collaborating with music producers.

Life and Work Balance

15:05 to 17:09

Tom discusses his daily work routine and involvement with various initiatives.

“The main thing I'm doing these days is promoting this book.”

Afghanistan: A Personal Journey

17:10 to 19:17

Tom shares his first experiences in Afghanistan and its cultural beauty.

“So now you kind of pivoted that to educational stuff for the Afghanistan people?”

Hashish and Hospitality

19:18 to 21:37

The conversation touches on the local customs and cannabis culture in Afghanistan.

“I spent a year on the road with two changes of clothes.”

Business Ventures in India

21:38 to 23:24

Tom recounts his entrepreneurial efforts and living in India.

“And she said, well, I'd been there for four years.”

The Evolution of Media

23:25 to 27:48

Tom reflects on the changes in the media landscape from the 80s to now.

“I mean, I've been out in the Hamptons, but I like a good beach.”
Show all 31 chapters

The Challenges of Accurate Ratings

27:49 to 28:00

Discussion on the accuracy of Nielsen ratings in the current media environment.

“And from there, it was just a question of how do you manage your business going downhill?”

Shifting Media Consumption Trends

28:00 to 29:22

Explore how cable's decline and social media's rise have changed media consumption.

“As cable homes dropped off, more people, particularly younger people, were moving their time in media to the internet and various websites and so forth.”

The Challenges of Data and Ratings

29:22 to 31:35

Discussing the inadequacies of current ratings systems and podcast metrics.

“I mean, even if you're like a guy with 600 Instagram followers like me, you get all this data.”

Podcasting and Personal Media Consumption

31:35 to 35:20

Insights into podcast listening habits and personal media consumption preferences.

“So, so eBooks and audio books are anywhere from 30 to 75 % of the amount of books they sell these days, which is, you know, the hardcover books are like a dwindling species.”

Podcasting and Personal Media Consumption

35:41 to 37:22

Insights into podcast listening habits and personal media consumption preferences.

“It's a really easy way to shop, and it's one of my favorite fashion resale marketplaces.”

Gray Areas in Business and Media

37:22 to 42:00

Examining changing legal loopholes and the state of the entertainment industry.

“Okay, so we've got a lot of weird government shutdowns and things happening in the world.”

The Impact of Change in the Entertainment Industry

42:00 to 44:24

Discusses the evolution of creativity and consolidation in the entertainment industry.

“and the word clever struck out at me as we could use a few more clever folks in this whole world and industry.”

MTV News and Its Cultural Significance

44:24 to 46:29

Reflects on the importance of MTV News and its impact on music culture.

MTV's Evolution and Reality TV Influence

46:29 to 48:57

Explores MTV's transition to reality TV and its effect on music programming.

The Rise of Streaming Services and Content Packaging

48:57 to 51:03

Examines the current landscape of streaming services and the need for better content packaging.

“and New York on board and spread the good gospel about it.”

Personal Journey and Career Reflections

51:03 to 55:46

Shares personal anecdotes and insights on a unique career path in media.

“And now there's so many streaming services.”

Meeting Fidel Castro and Cultural Exploration

55:46 to 56:00

Recounts an encounter with Fidel Castro and exploration of Cuban culture.

Cuba and Castro: A Surreal Encounter

56:00 to 58:09

Learn about a filmmaker's unexpected lunch with Fidel Castro in Cuba.

“And when we get there, you know, it was 2001, you know, at the hotel, you know, you had the Lucky Luciano suite.”

The Price of Diplomacy: Fines and Legal Battles

58:10 to 59:16

Discover the legal repercussions faced after meeting Castro.

“And I got a letter saying, you went to Cuba, you had lunch with Fidel Castro, we're fining you$55 ,000.”

Dining in NYC: Favorite Spots and Experiences

59:17 to 1:02:15

Explore favorite dining spots in New York City and their unique vibes.

The Rise and Fall of Vice Media

1:02:16 to 1:04:39

Analyzing Vice Media's journey, successes, and failures in the industry.

“And in his heart, he really wanted to, you know, not just entertain, but like inform young people and take them to different corners where, you know, mainstream media wasn't covering it.”

Investments and Missed Opportunities: Reflections

1:04:40 to 1:08:28

Discuss the challenges and mistakes in media investments and ventures.

“You know, they, it was a continual process, but I, I got options in the company and I helped connect them to other people.”

Rupert Murdoch: A Complex Relationship

1:08:29 to 1:10:01

Unpack the dynamics of friendship and competition with Rupert Murdoch.

“And this guy, Saad Mohseni from Afghanistan, came to see me.”

The Importance of Personalities in Business

1:10:01 to 1:12:03

Explore how personal relationships impact business decisions and creativity.

“No, I think that wives will bring you together with people maybe you wouldn't, you know, maybe you'd sit across the table from in different scenarios.”

Favorite MTV Unplugged Moments

1:12:04 to 1:14:32

Delve into memorable moments from the MTV Unplugged series, highlighting favorite performances.

“obviously a reference to the mtv unplugged series maybe not a complete inspiration for it but of all uh of all the unplugs over time what has been your favorite episode oh there was a few LL Cool J.”

Bob Lefsetz's Impact on Music Journalism

1:14:33 to 1:14:58

Discuss the influence of music critic Bob Lefsetz on the industry and its journalists.

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Transcript

Automatic transcript. May contain errors.

0:17Tom Freston:How long gone? It is an overcast rare Thursday recording. We've had to adjust our schedule because we have the GQ Man of the Year awards tomorrow night. I'm in Los Angeles and so is jason i gotta say big bro i needed i needed sun and i'm not getting it and i'm not gonna get it

0:35Jason Stewart:from what i understand a little rain tomorrow like i said you just missed it bro 87 degrees yesterday or whatever it was so you you're at the chateau and our listeners should know your your suitcase with your podcasting equipment is being held hostage because they're setting up a red carpet in the little area for some dumb event tomorrow so that that's why you hear chris's voice i don't think it'll sound i don't think it'll sound that bad to be honest i don't i don't i didn't say it's going to sound bad i'm going to say it sounds different

1:04Tom Freston:different i well the the yeah the um i ran to will in the lobby and he was like yeah we're getting um they're saying it's an atmospheric river vibe tomorrow so we've decided to make we've decided to make a few changes to the layout to make sure everything's covered um but you didn't see a river i forgot about that phrase it's such a great descriptive term it really says so much uh but he seemed he didn't seem stressed so i'm not stressed you know yeah we'll throw a little

1:31Jason Stewart:money at that problem you know it doesn't have to be all indoors i mean all outdoors right no it doesn't it really doesn't yeah i'm excited after this i'm gonna hop in the sauna head over there we got some table reads feeling very writer's roomy i can't wait to get the uh the checks mix going on the whatever we or the sweet green orders protein plate don't worry i already i

1:54Tom Freston:already ran into 15 producers uh that said hello um that i recognized from our zoom calls so they're walking they've got the gummy they got the gummy worms out in cups already somewhere somewhere in

2:05Jason Stewart:this fucking are you a red vine or a twizzler household oh that's why the motherfuckers get

2:11Tom Freston:fat the writer room don't pay enough to put on 20 for meeting all the snacks you gotta like that's they should give you the option is GLP-1 or snacks. You can't do both.

2:20Jason Stewart:GLP-1 or PB &J. Whichever one.

2:23Tom Freston:That's it. In the writer? I see that all y 'all do is eat. That's all you do. Writers, I feel for you. I know it's tempting. I have the same. Look, you put your cheeses in front of me, it's going to be tough. Don't leave them around you.

2:34Jason Stewart:Don't leave your cheeses around me. True eater for real. Chris, famously known as a real eater, of course. Yeah, sorry about the web. I'll be in New York this weekend. DJing a wedding prayed it let's pray that we go wheels up I feel good about it though I'm not

2:51Tom Freston:worried about it I honestly did I mean I honestly it was business as usual today it's a crap and it was busy like it was busy like it was you know it wasn't it didn't feel different in that way

3:01Jason Stewart:but yeah I the not a lot of crying not a lot of people sleeping on cots and and waiting bread

3:07Tom Freston:lines or anything like that no but there's there's a lot of um now that winter's hitting i think people are trying to put those masks back on and oh you mean because it's like uh

3:19Jason Stewart:cold season cold season what a little you know what jason it's shocking to me that people don't

3:24Tom Freston:i trust my immune system i feed my immune system i'm nice to it i coddle it i keep it warm i cool it down if you take care of the system it should work fine you know like obviously there's there's other factors involved but i just noticed like i went to the uh wednesday show last night at brooklyn steel and of course there were some masks in that audience you already yeah you already know

3:46Jason Stewart:there's a man but that audience they got a mask that ain't even out yet up in that page

3:49Tom Freston:again the new shit they got but there was a i saw i saw a lot of masks at that show but also the people wearing the mask and this is disappointing closer to our age than college age

4:02Jason Stewart:when i went to that all ages electro clash yeah and slow dive festival i saw a lot of people wearing masks it was it was really but it was like one or the other there was no gray area yeah yeah yeah like like with adulthood it's really all over the place and some people are are hypochondriac-y than others and some people have actual illnesses and blah blah blah but when i was there it was either like i have an emotional support backpack that's also a panda bear and i have my mask and i have my earmuffs and i have my yes you know when like the horse they have to wear the little thing on the horse so they don't get spooked from the side they got that shit on it's either those people where if you like walk past them they go like just by like being in or it's either that or just people like puking on the floor or just like what up dude my name's brad you guys want to like fuck later i'm wearing a wearing a tank top and have a sepna piercing

4:55Tom Freston:and smoked a whole pack of cigarettes i don't know what day it is yeah that is the i brought my dad here he's chill that is sort of the that is kind of what a lot of shows are like now i think

5:05Jason Stewart:that that divide but i but i like that everyone with young people at least everyone gets along and no one is oh yeah yeah no one is i mean it's different if depending on the show at a wednesday show it's a lot of nice people probably less right-wing conservative i would say zero of that i live maybe very respectful of everyone's space it wasn't actually you know i was standing i was

5:29Tom Freston:standing in a little balcony and they weren't super respectful of my space if i'm keeping it 100 with you i think they were like this big cis bitch is in my way i can't see i just i was kind of trying to keep my little spot as the show started i felt like i was getting a little they were encroaching i feel like some baristas were edging me out when when when we were at the

5:47Jason Stewart:addison ray show in the balcony if somebody tries to encroach guess what no no dice you got to crawl down on your head chase suey wonder's got to crawl down on the floor hands and knees luke gotta sniff

5:58Tom Freston:my nuts if he wants to see s and ray and he might like it that's the fucked up okay over a wednesday you're saying they felt a little more entitled they felt entitled and i i i and i mean you suffer from this way more than i ever would but i i am uh aware of my size and that i am probably obscuring

6:13Jason Stewart:someone's view and i want to be respectful of that earth master over here yeah i want to be

6:20Tom Freston:respectful of that because you know they paid the money to see the band they love you know as much

6:24Jason Stewart:as i did so i want to donate to greenpeace too i want to do a lot of shit chris i wouldn't do that

6:28Tom Freston:no don't don't put that don't put that on my jacket big but all i'm saying i want to see what

6:32Jason Stewart:happens at a show that has a little more rowdy energy you know what i mean or i want to see some i want to see you rip someone's n95 off in the pit oh don't worry when american nightmare plays

6:45Tom Freston:at rough trade record store i'm about to go fucking crazy don't even worry about it there's no mass i don't think there's any mass there but i went so before the show jacob and i went to bernie's i'm sure you've heard of bernie's it's a restaurant green point and i'd been there once or twice for an event and i i have to say and i told the owner this but second best veggie burger in the world maybe after after houston's really it was yeah it was and i it was very very good

7:12Jason Stewart:i was really impressed so does it go houston bernie then superiority i i love superiority

7:19Tom Freston:sandwiches the burger isn't my favorite thing do you know what i'm saying like the sandwiches are so good there's a lot of them that are really good but the the burger is fine this burger was multi-patty and exactly and it felt it just felt like are you saying more than two i think it was two but with shredded lettuce american cheese sesame okay standard standard no very no funny

7:42Jason Stewart:shit no funny shit no fig jam no blue cheese but i told i told all of her i was like brother this

7:47Tom Freston:thing is really fucking good the fries every it was just it was a great what farm was the shredders from you know what i am an inquire about that because i was like bro is this shit all vegetables he's like he looked at me like yeah you fucking idiot of course and like look i don't know man there was do you remember how popular fake meat was for like a three-year period i feel like it

8:04Jason Stewart:was but it's over it's like kind of over yeah i mean i still see impossible every once in a while

8:09Tom Freston:but it feels very it's giving phased out i'm referring more so to beyond i feel like that was a fucking rocket ship and then it just fucking people were like wait this is actually

8:18Jason Stewart:terrible for you i don't like i'm not gonna eat this a lot of a lot of undigestible gluten yeah

8:23Tom Freston:in play look i was i made the truck to brooklyn last night and it was a success all around and

8:27Jason Stewart:that makes me feel great okay you've been doing good over there in brooklyn lately bopping over to tame we over at strange delight now bernie's with wednesday i saw i saw strange i saw strange

8:39Tom Freston:delight guy at allison roman's book party and i but i didn't get to say what's up to him and i I was like, oh, that's my... He's wearing the hat, so it was a giveaway, but good restaurant. Good guy.

8:48Jason Stewart:Okay, well, the next time I'm in New York, we can try to do one more cool... We'll do a noodle pudding and...

Read the full transcript

8:56Tom Freston:I'm ready to go. If I have to hear about it one more time before I eat there, I might kill myself, but I'm going to eat there.

9:01Jason Stewart:I don't care if Jack Antonov lives upstairs only because Lena used to go there.

9:08Tom Freston:I'm going to go up on Jack. I'm going to knock on Jack's door and be like, all right, let's see what you really got, bitch. I want to hit. like let's get in here i want to get in the i want to get in the lab not a not a fight you want him to write a hit okay my my i've had a long i thought you meant like i'll let you have first punch no i mean i would let him have first punch it ain't i can take a little the photo of margaret sitting

9:26Jason Stewart:on his lap where he's wearing the the nba basketball shorts and the wife beater a lot of

9:31Tom Freston:people are like you guys don't get it this is the perfect this is how all jewish couples they're like this makes so much sense actually you don't understand i was really he's been pulling like this since day one yeah i want to i want to go knock on it i think that's an idea for us too is that we show up at emil's house or mark gronson's house or jack antonoff's house like all right all right wyatt andrew wyatt we got 12 hours let's let's see what we got let's see what we

9:54Jason Stewart:can do so it's a little scared straight exactly sabotage it's a little room raiders yeah it's a little i'm gonna do the white glove test on the ns 10s please believe now you know i'm not white gloving anything in a meal's no no no no no no but yeah i think this is this is an idea i've had

10:12Tom Freston:for a while where i'm like how good these i think of these guys as geniuses that are such a big part of the process and really are the ones doing it but like if you and i show up at tobias jester jr's fucking farm and you're out picking carrots and i'm like all right what do you got bro oh

10:27Jason Stewart:olivia dean can do it but i can't i pull the mpc out of the suitcase and say start cooking i feel like fred again would be able to do this more than almost anyone else because all these other people it's kind of like showing up at jack kerouac house and be like all right give me a

10:43Tom Freston:nice little story about the american struggle off top i need i need i need a 2 000 word story about

10:49Jason Stewart:the american struggle on site like right now mozart i need a verizon jingle my desk sundown there's an extra 1500 in it for you if you can give me the stamps oh god that's so fucking funny

11:02Tom Freston:it's so good uh all right yeah so anyway we're here watch us in the live stream tomorrow what

11:06Jason Stewart:time is live stream yeah 7 p.m pst if this comes out before then thursday night 7 p.m pst on the

11:12Tom Freston:live stream hopefully we'll cut it up for youtube we're gonna be talking to all of our favorite men and uh women additionally of the year gotta give it up to the man thank you to our gq family uh will welch for for inviting us to do this we're happy to be here uh i think that's it jason i'll so you're in a couple hours for uh more uh reading do you still want to get dinner after

11:33Jason Stewart:our table read just to keep it all the way hollywood with it we should and there's also

11:37Tom Freston:some uh there's some partying happening at one of your favorite places that has also been uh added

11:43Jason Stewart:to the slate just if you're interested slate for tonight yeah yeah a little pre you know a little something something light i have a facial at 8 45 how's this gonna work yeah that's the whole point

11:54Tom Freston:it fixes it, the problems

11:56Jason Stewart:I'm so glad we had this convo what's the party? I'll bleep it

11:59Tom Freston:got it I think Jake's going to be here so we'll see, I'm going to feel insane

12:06Jason Stewart:is this a USB situation for me?

12:09Tom Freston:does Asad use vinyl or does he use USB?

12:12Jason Stewart:I think he can handle both

12:14Tom Freston:go bump him in his silk shirt out of the way and see what you can put a little Madonna on for the heads

12:18Jason Stewart:I'll blaze Asad a little ass tonight

12:21Tom Freston:No, thank you guys for listening. Howlonggone.com. And we'll see you on the World Wide Web. Thank you. Log on. This episode of How Long Gone is brought to you by a new podcast from The Guardian, stateside with Kai and Carter. This is covering a lot of our bases, Jason. It's trying to slow down the news and wrestle with the questions we all have about what's happening in the world. And I know you particularly have quite a lot of questions.

12:47Jason Stewart:A lot of questions, but how often? Because we do this podcast three times a week, and that's a sweet spot. How many times do they do?

12:52Tom Freston:Three times a week. And I have a feeling, just based on the platform and these talking points, that they're maybe going to be covering different stuff than we do. That's just a guess.

13:01Jason Stewart:The Guardian is not some billionaire-owned platform. They're not afraid to say what they want to say, brother.

13:07Tom Freston:Yeah, Rupert ain't sniffing around in what journalists Kai Wright and Carter Sherman are up to over there at Stateside. But yeah, listen wherever you get your podcast. You can watch it on YouTube. It's three times a week. And who couldn't use more news? You know, especially when it's not, you know, from here, let's say. Give it a listen. Give it a listen. All right, this episode of How Long Gone is brought to you by Revolve. I don't know if you've been paying attention, Jason, but guys really be caring about how they dress and how they look. Luckily, Revolve, man, is on the internet, super easy, and it's stocked with some of our favorite brands like Ralph Lauren and something maybe you like, Fear of God Essentials.

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14:05Jason Stewart:Yeah, it's true. And that two-day shipping really is nice. It really does happen. I've used it a few times and it is surprising how nice things show up and you get excited to try them on. It feels like a luxury shopping experience versus somebody just throwing your shirt in a bag and kicking it down the hill. So whenever it's a big night out, a wedding, a trip, or you just need something last minute that actually works, Revolve Man always has it. Go to revolve.com slash howlong to shop and use code howlong for 15 % off your order. Free two-day shipping, easy returns. It just makes things easier.

14:41Jason Stewart:That is revolve.com slash how long promo code. How long 15 % off your entire order this offer and soon. So do not sleep on it.

14:52Tom Freston:All right, Tom, look, thank you for joining us on how long gone. Are you in your study? Is this an office? It looks like this is where I work. This is my office, but it's in my home. I'm in Manhattan. I'm in New York. So I'm just working a worker bee here. Sure. sure so you don't you don't need to at this point in your life you don't feel the need to separate sort of uh home and work with an office that you have to commute to you're happy to stay at home it's a mixed blessing for those of you with home offices when you used to leave it oh that was like a punctuation mark leaving the office and you know yeah when you have it in your house it's sort of like you know a monkey on your back you know you can always dwind back in there but yeah it's convenient yeah it's an easy commute if nothing else are you uptown are you an uptown guy i'm an uptown guy now i lived in tribeca for like 20 years but i moved uptown and uh here i am okay

15:44Jason Stewart:you so you you described yourself as a worker bee at this point in your in your life and career what are we diligently working away at you know there's an old maxim that work will expand the fit the fit the amount of time you had if work was always your default position. So I do a bunch of things. The main thing I'm doing these days is promoting this book. But other than that, I've been the board chair of this thing called the One Campaign, which is a stand-by poverty advocacy group, focuses on Africa, does red. Shout out to Bono. Yeah. So I've been doing that. I'm the board chair for 18 years.

16:22And in the wake of a lot of the Trump cutback, I'm really busy. That takes up a lot of my time okay uh i've been working with these tv networks uh in afghanistan i went back there and they're still trying to see how we can solve it yeah i want to get into your

16:40Tom Freston:relationship with afghanistan because i think you're the only person i know that has been there

16:44Jason Stewart:voluntarily let's get the charity stuff out of the way at the head at the beginning time well that is charity stuff because i'm working there for free you know i know i'm i was helping them set up the first commercial thing after the fall of the Taliban. And the idea was this was going to help build tolerance. They never really had television, help socialize and civilize people, connect them to each other, all of that. They never really had television. No, no, no. So now you kind of pivoted that to educational stuff for the Afghanistan people? That's right. No politics, just math and stuff, I'm assuming.

17:20Yes, that's right. And we had like 250 advertisers when things were booming. Now there's one. Okay, so we cut the ad rev. It's like Red Bull. Red Bull. Because it's like these energy drinks because there's no alcohol. People just want to get jacked up doing stuff.

17:38Jason Stewart:It's a little cardamom Red Bull or whatever Zoran's drinking. That's what they're selling ads for. They have their versions of the Red Bull. but it's that we get money from foundations like malala and gates to do educational programming for afghan women who've been marginalized you know when's the first time you went there though like the 60s i went there in 72 i went there in 72 and fell in love with the place but you were just on like a vibes mission at first i was on i was on a vibe mission i was what was her name tom what was her name susan susan got it a famous afghani name susan no i was advised to go there i was i was uh i had been in advertising in in this in new york work they had tried to get me to work on charman toilet paper and i got quit that was the last straw for me and i went at this woman said come and meet me in paris we're going to cross the sahara desert i did that stayed with her a couple months and then i kind of went everywhere and then i met this susan in greece who told me, India, that's like the Holy Grail, the greatest show on earth.

18:43So I went overland and stopped in Afghanistan after being in Iran and Lebanon and so forth. And I just got a fascination with the place. It really struck me. It was beautiful. People think of Afghanistan now as this barbaric place where everybody's fighting all the time. But back then, I mean, they had a tourist poster. They didn't have any tourists, but you say, visit Afghanistan and see the world's friendliest people.

19:04Jason Stewart:And you can attest to that. You agree that they are the friendliest people. i did it was they were very hospitable it was a beautiful land it was exotic it was like i was stepping out of time it was intoxicating okay what did what was your look at the time i was a little hair i i had a different haircut you know i imagine the hair was a longer but was there any

19:25Tom Freston:what was the look as far as the the tattered rags yeah i'm imagining a jay peterman from television

19:32Jason Stewart:in Seinfeld, you know, trekking from Manhattan to Timbuktu? I spent a year on the road with two changes of clothes. So by the time I got there, they were a little ragged, but you know, I would pick up clothes along the way. Okay. So we were traveling. We're traveling light. I was traveling light with a duffel bag. Yes. Okay. Hitchhiking down the Silk Road. I did. I hitchhiked there. And what was the Hindu Kush looking like over there in Afghanistan at the time? Well, they were always like 20 ,000 plus foot mountains covered with snow. They were beautiful. There was no pollution because there was hardly any cars.

20:07Now it's a whole other story. I'm talking more about the Kush. Oh, the Kush.

20:11Jason Stewart:That might have a little crystal on snow cap, different kind of cap on the mountains. Afghanistan had the best hashish in the world. And they were proud of that. And it was called, but no one called it Hindu Kush. It was a Kush variety. That kind of came about when those California botanists got into it, you know, started naming strange. Wiz Khalifa took that and ran with it, didn't he, Tom? They did. Hindu Kush had a whole new name, but it was very relaxing. And they would sell it. When I checked in at immigration going across the border, they said, you got to stay here at our hotel because it's too dangerous to leave.

20:48And then the guy at the government hotel, I changed some money. And then he said, you want hashish? And he holds up all these little disks. He says, you know, we have the world's finest hashish. I said, isn't this duty-free? He's going, duty-free. I go, you know.

21:05Jason Stewart:Is this a fucking trick? We're at a government building. You're selling me hash? It was everywhere, yeah. That was a good part. So that sounds like when I go to San Francisco, they say, here, welcome to the hotel. Don't go outside, though. It's not safe.

21:17Tom Freston:Yes. We'll keep you indoors, but occupied.

21:19Jason Stewart:Okay. So final verdict, the hash is quite relaxing, but you don't really partake anymore, I'm assuming? or or who knows no i do i do okay my man you know whenever i find the time you're you're a real lifer i appreciate that that's commitment yeah and inspiration to me because you you look great and professional and successful and if you're still smoking some pot what an inspiration well a little a little here and there is a good for you know it's good for you for your mind brother

21:48Tom Freston:i yeah it feels like it informed your approach to life a little bit but you didn't let it uh let's say to take over like some people might no i've seen that i've seen that i've seen that i was

21:59Jason Stewart:i was a light user sure good good good half a joint max well as somebody who came from the advertising world knew how to sell one or two things when you touch down and you see all this going on over there were were the the alarms ticking in your head of of opportunities of how you could sell this stuff back to americans yeah well first of all i i met this woman in greece and she would show up at these beach cafes and she had trunks of clothes and she lived in Kathmandu in Nepal. And she said, well, I'd been there for four years. She was an American and she would make her own clothes and then ferry them to Greece and Italy and sell them.

22:35And I saw that and I said, wow, that's interesting. I could do that. What about if I could do that on a grander level, make, you know, sell to stores and it would be what I was really looking to do is find a way to support myself over there so I could live there and travel because I was just totally engaged with it was crazy over there in those days it was really you know you're really living life on

22:57Tom Freston:the earth would you would you call it lawless is that fair to say well i had i wouldn't say it was lawless no i'm afghanistan afghanistan my main business was in india which was then you know sort of the greatest show on earth crowded and crazy and sort of a socialist incarnation but it was it was the hardest work i ever did in my life but i bought i got a house in delhi and i wanted to live there so i started this business and it became quite lucrative you rented so how was it easy as an american to come in there and just rent a house if you had cash or buy a house if you had cash no they were very very paranoid of foreigners and today if you're american go work there but in those days the indians were you know newly independent paranoid about foreigners getting out of colonialism all that but i'm my agent i found a partner in india so he would rent the house for me we would live there and uh you know you could live quite a nice life it wasn't that expensive it was really you could live like a pasha yeah but uh built the business and it grew and grew and it was a lot of fun and i got to travel everywhere and you one of your first

24:02Jason Stewart:account or like big scores was was getting the bloomingdale's account and we had gene pressman from the barney's family on a month or two i listen i listened to that i listened to that podcast yeah so was he was in palm beach yeah he's down in palm beach he he gave up you're still you're still fighting the good fight yeah he's on the bench down there it's on the bench he he needs a little bench time but i guess my question was was there ever a desire to be into barney's or did you want bloomingdale's more than barney's was there a bidding war or do you do you know gene and in those days barney well yeah we were in uh like most of the macy's bondwood teller which is now the trump building uh macy's barney's then was largely on seventh avenue he probably explained it to you in his early incarnation selling discount suits so it wasn't really the player

24:54Tom Freston:that gene made it to be at that point okay do you have a relationship to palm beach i feel like you really said it with some uh pizzazz in your voice no i don't have any it's i'd much prefer california than to be a florida man okay yeah i would have to agree with you so you're saying if you need a little R &R, you would rather go to California or are you like a Hamptons guy? I'd go to California. I mean, I've been out in the Hamptons, but I like a good beach. They have lovely beaches, little traffic jam out there.

25:23Jason Stewart:Sure. Well, yeah, Chris just flew in from JFK. He's at the Chateau Marmont right now. Is that where you stay or do you stay somewhere else in LA? Well, I had a house there for a lot of years and I sold it. Before that, I used to stay at the sunset marquee and then when i was on expense account i used to go to the hotel bel air in the olden days and now i'm sort of in in between hotels when i go out there i don't know where to stay i generally stay with a couple of friends yeah i feel like your friends have houses bigger

25:51Tom Freston:than my friends so there's you know you kind of have your own entrance maybe you know there's it's a little it's a little easier to bunk up with the homies if you feel like going all the way over malibu yeah i uh i i have some friends who have some money but i also have some living closer to the ground like you guys thank you for noticing within 15 minutes that we were living

26:09Jason Stewart:closer to the ground you got a moonvez on the top you got a green card way down below you're at the chateau out there you know that's pretty cool i've stayed there a bunch of times i love the chateau

26:20Tom Freston:it is cool it is it is uh it's also an expensive hotel in its own way but the bel air is a very special that feels like its own planet i've never stayed there actually i've only been for like lunch but it feels very removed it used to be nicer they closed it for three years to renovate it and modernize it so i would find a trend whenever a hotel that was nice and kind of unique and had wooden floors and then they redo it and everything has a marble floor it's generally loses the vibe the charm is gone for sure they can charge more somehow they always find a way to charge more

26:51Jason Stewart:yes that's not a problem okay well you you said you were coming back here on on the expense accounts way back in the olden days and oh you're obviously exaggerating a little bit but what in your mind it seems like you were in that perfect time where the getting was good the last great moment of of the media entertainment world if you could put a year like around what year did the the media landscape kind of stop being a fun place that was ascending versus the the you know Whatever it is now. The 80s and 90s were totally key. I mean, the 80s had the beginning of the cable TV revolution, and that kind of carried through big time right on through the 90s.

27:33So MTV, Comedy Central, all the cable networks were really like cash machines. And then we began to see the decimation of that as the digital revolution began in the early 2000s. And I'd say I left in 2006. And that's when, you know, YouTube had launched in 2005. Facebook was just getting going. And from there, it was just a question of how do you manage your business going downhill? As cable homes dropped off, more people, particularly younger people, were moving their time in media to the internet and various websites and so forth. And then social media came along. And it's been tough sledding.

28:16Tom Freston:you know you know i want to ask you a question about nielsen uh the ratings system because i i want i feel like that was accurate and now everything we get is not accurate is that fair to say i i think so i mean i don't know what their methodology is and i don't know how they can keep track of everybody's on phones and they're uh you know they're you know you just don't know where it used to be easy when you had three networks to meter and then you had 35 cable networks they thought that was complicated now it's like infinite fragmentation and um you know there's smart people there and they're trying to figure it out and i haven't kept that close track of it anymore but i would imagine it's not as accurate it used to be you know they can add up the traffic on websites and so forth and aggregate it but and on podcasts podcasts are easy yeah like you guys you guys know exactly how many people download you and how long they listen right yeah i can't count that high thankfully but yeah it's yeah those are box car box car numbers

29:17Jason Stewart:exactly exactly we got their genders we got their pronouns we got it all tom i would say the data

29:26Tom Freston:we get is maybe too much like there's data i don't need like i just want an uh i don't like data i don't care about it but i want one number that feels successful like we should like podcast

29:35Jason Stewart:should have one like fico credit score to show the overall health and quality yeah exactly That would be good. Yeah. I mean, even if you're like a guy with 600 Instagram followers like me, you get all this data. I mean, and what am I going to do? This is more data than I used to get running a cable network.

29:51Tom Freston:Well, Tom, luckily for you, the trend now, it's considered hot for a guy to have low followers. So you're kind of, you're at the forefront. Mine, you know, they're probably dying off of old age and it's dwindling. I need new users, but maybe it's good there. i get down to one or two people yeah you get all the way let's see i'll be like totally analog yeah just one one person is all you got left one person yeah i mean podcasting is what is your podcast digestion do you do you listen a lot or no i i don't listen as much as i'd like to because i don't really have these moments where like i'm driving a car or um you know yeah but i i do smart lists i've listened to a bunch of yours i do walter isaacson i do some science stuff i do stuff to the daily and things like that but i don't i don't sure i don't listen to podcasts or audiobooks as much as most other people do so you're not walking the dogs you're not i don't have a dog to walk or i'm not smoking a dog walker or however that goes and you're not you're not a

30:56Jason Stewart:ton of dish doing every night and you know taking the trash out things like that no gonna clean out the garage not a lot of i live by myself i don't have that much trash damn bro really tom you're

31:08Tom Freston:living the dream man all right you live alone you got no dog you don't do dishes no i don't do

31:13Jason Stewart:dishes your doorman listens to your podcasts for you probably i don't know if it makes me a bad

31:19Tom Freston:person but uh you know i think that all of our media consumption uh really is dependent on sort of age and habit and how willing you are to break those you know or modify those after years and years of doing it a way that works for you. Yeah. I've been surprised. And I talked to my publisher. This is my first book I had out. So, so eBooks and audio books are anywhere from 30 to 75 % of the amount of books they sell these days, which is, you know, the hardcover books are like a dwindling species. I said, where the hell do people have time to spend 13 hours listening to somebody's book? You know, it's hard to just whiz through it.

31:55Tom Freston:I look, but they do. I don't, I don't have a car. So I tried an audio book one time and I just was like, yeah, you know, I totally understand it and I think it's efficient, but it just didn't feel the same.

32:06Jason Stewart:Yeah. I like a biography or a memoir for the audio book while I'm, while I'm working out. That's what I like.

32:11Tom Freston:It's also, if it's read by the author, it's kind of interesting. You know, that makes it nice. I feel like it feels, you know. Well, you got to get mine then, you know, 11 hours of me, you know, you only get in one hour.

32:22Jason Stewart:I can knock that out on a weekend with the kettlebells, Tom. No problemo. You don't listen to music. I mean, at work out, you got to listen to some upbeat music. So I guess. No, no, no. I'm already upbeat. And once we get to the SmartList level, we'll be able to get the copy of the book and we can read it before we have you on so we can talk about your rich life and history. But it is an honor to be talking to somebody who was on SmartList the same week, which means that we've closed the gap between our sworn enemies.

32:50Tom Freston:We consider, Tom, we consider Smartless the enemy because they're doing exactly what we do, but they're rich from it. And it's sort of a, you know.

32:59Jason Stewart:Just a few guys talking about some bullshit, and they happen to be very rich. I'm thinking this is the greatest job in America. They're getting$100 million deals, no set, no hair, no makeup. No jokes. It's all there. Like you guys. They say they're working in their underwear, and I can see you guys are too.

33:19Tom Freston:well look when we get when we get two different hundred million dollar deals my underwear is

33:22Jason Stewart:going to change too it's going to be a whole different me yeah but but when they finish their their viory underwear podcast they go out and play golf and get lunch i'm in the trenches i have the episode fired up he's doing the booking i'm doing the post-production we're we're promoting it ourselves so we're in the trenches for the little guy you know we're like you selling clothes in india for year one you're in the trench at the chateau look hey look i'm saying there are some

33:49Tom Freston:perks i'm saying some perks but we don't fly private i just want to put that out there you know this i got that feeling all right jason this episode of how long gone has brought you by superpower and i don't know about you but i'm sick and damn tired of leaving the doctor's office uh feeling like i got no useful info from these bozos you put on the white coat you sit down you say a bunch of stuff but it's nothing i can use you know maybe you told me you're fine drink more water as if i could uh i i'm not leaving with with no no real data no game plan just a pat on the ass and and i'm sick and tired of it and luckily jason's superpower

34:25Jason Stewart:is here to fix my problems yeah sometimes i feel like i'm the only one who really cares about inside of my body and all the diseases and now you know the doctors they've been gatekeeping this info and they don't really care about me that much. Their head is out of the game. They're thinking about golf. They're thinking about what they're going to have for dinner. I care. I want to go through all these tests, hundreds of data points here, and I'm ready to go in with my internet research and really find out what's going on with my body and how to fix it, how to help it because we don't know what's going on inside of our body.

35:00Jason Stewart:We don't know how much sleep we should be getting, what supplements we need, what foods we should be avoiding. And this info is all there thanks to science and technology. So make this year the year you stop guessing about your health with superpower. For a limited time, our listeners get$20 off to unlock their new health intelligence. Head over to superpower.com and use code how long for$20 off your membership. That's code how long. And after you sign up, they'll ask you how you heard about Superpower. Do us a favor if you could and tell them Halongon sent you, and that'll help support the show.

35:37Tom Freston:All right. This episode of Halongon is brought to you by Poshmark. Jason, I know you've used this site before. It's a really easy way to shop, and it's one of my favorite fashion resale marketplaces. I don't know if you're into brand names. I can be, depending on how I'm feeling. But you want to talk Levi's? You want to talk Blundstone? or you want to talk chrome you want to talk prada you want to talk mimi you want to talk botega we got it all at poshmark and you can you can get the look uh for less as they say yeah

36:06Jason Stewart:i'm a big hunter i like going on ebay and digging around and sometimes stuff isn't there same thing with carol and my wife she's a wardrobe stylist and she's like you know the real shit's on poshmark for the real heads that know you can find those you know little grail pieces that you can't find anywhere else, some kind of archival stuff going on, but also, you know, the day-to-day regular kind of staples, like you're talking about some nice vintage Levi's, tons of them over at Poshmark. And, uh, you know, when you're ready for a closet refresh, you can earn some real money selling the pieces that you're ready to part with reaching more than 80 million users on the platform.

36:45Jason Stewart:I like that sound of that, Chris. What is there something that you're trying to track

36:49Tom Freston:down on poshmark specifically i'm actually in the market for a new adopt kit a secondary dop kit second backup probably lv to keep with my my suite of products or maybe a prada nylon um because that that's also very uh durable okay i feel good about it but uh because new deals

37:08Jason Stewart:and styles are listed every single day so do not wait download the poshmark app today use code how long when you sign up and get$10 off your first purchase. Okay, so we've got a lot of weird government shutdowns and things happening in the world. A lot of things that you used to do and be able to get away with, you know, tariffs and international importing and exporting and a lot of gray areas and legal loopholes and things like that that you've been able to sort of skirt around and take advantage of in your lifetime after seeing all of that go down what do you think the next kind of gray area or like little fuzzy loophole area is going to be the next to crumble in our surveillance state you're a loophole for what just anything anything legal you know just like how we used to be able to do all kinds of stuff and now we can't at all you know i don't know it's kind of a dark time

38:04Tom Freston:that's right you know people keep saying this i went to jfk this morning i had no problems at all fully staffed and i feel like i keep hearing these horror stories on the internet but no one i haven't heard one from a human being a human being mouth you know i look at the news i got like these lines going out the door and around the corner of some of these airports it looks like it's a nightmare i haven't been flying i'm supposed to fly next week so i'm a little terrified that uh i'm gonna be in one of those lines outside i think it's over i feel like it's over to some extent what is your did you build with trump back in the day i feel like you guys are probably crossing paths trump's

38:35Jason Stewart:the news today right not not in a business sense just in a nightclub sense you know not in a business sense just in a party an epstein party yeah you know just a chill no i i i didn't really know trump i don't really know trump uh very well he used to always call up and want tickets to the video music awards or the vh1 fashion awards and we'd take care of him and he sometimes he would send me a note with that you know you'd see that signature and no idea the guy's not a

39:00Tom Freston:lot of bad but the signatures for all of his fault that's maybe it's strong maybe it's best work Yeah, the signature is amazing.

39:06Jason Stewart:That's his best work. Like a Japanese calligraphy master.

39:09Tom Freston:I just feel like the idea of calling you to get tickets to an award show that you have nothing to do with is such an ego move. It really says a lot about someone. Well, you know, it was the MTV Music Awards. He figured I was sort of Mr. MTV and, you know, why mess around? Go to me. So you give Donald Trump tickets. He was sort of a, you know, quasi celebrity. Yeah. He wasn't a real favorite in New York City, you know. No, no, no. Still isn't, from what I can tell. I think he got 20 % of the vote the first time around. From what I can tell. But the MTV, I've been lucky enough to attend the MTV video.

39:45Tom Freston:Maybe, when did you say you stopped? 2006. Honestly, I think I went the year after for the first time. I think. I think. But I remember I used to manage a band, and I remember you looming large. Our TRL success was very important to the Epic Records family. and uh i i always found that trl was such a magic time that can never be replicated yeah i mean we had more of a mono culture then what was the band they were called cartel as in mexican as in mexican as in uh white guys from conures georgia but yeah as in venezuelan drug cartel that's right the word is spelled the same yes the word is spelled the same but that was the first time i ever you know we were in like the green room at trl and it was like you know us and soldier boy and you know and acting like natalie jonesa jones heart yeah it was just like such a strange mix of people that you could get in the same room and you're right though it like the audiences were all there was one audience so it worked well it was you know because you'd have all three or four different music genres kind of locked together which i always liked that's how radio was in the 60s you know am radio top 40 radio is all kinds of different music the rolling stones the supreme Now everything is algorithmized, how you might say it.

41:03Tom Freston:How were your relationships with the, like, what relationships were you managing the most during those MTV days? Was it with record labels mainly, or was it with just your team, or did you have to interface outside of the building a lot? Well, I, you know, we had to deal with the cable operators and satellite guys. There were distributors. Then there was the advertisers who brought the money in. Those two groups brought the money in. And then there was the music industry who gave us our programming. and I kind of always gravitated towards the music guys because they were they love music and I love music and we could kind of talk the same language they were fun they were clever and we need to have good relations with them because they were giving us these videos so you know my default was sort of hang out with the people who are more fun but I had exposure to me too you know how that goes right yeah if you gotta choose a side yeah I'm trying not to kick it with the cable programmers quite as much as the A &R guys.

41:58Jason Stewart:You said the word clever, and the word clever struck out at me as we could use a few more clever folks in this whole world and industry. You know, a lot of the creativity has been sucked out of the entertainment business at large in a way as companies consolidated and cost became paramount. And as these entertainment... You know, when we started MTV, there was 40 record companies. A lot of them were run by like entrepreneurs and who based on their taste. And you love that. You know, the Ahmed Erdogans of the world and so forth. Chris Blackwell. Now it's two and a half record companies, really.

42:34You know, big ones. They're all consolidated. So they, you know, they run more efficiently. But, you know, on one level, you could say maybe music isn't as vibrant. I don't know if that's true. But a lot of the outsized characters that used to exist that made the business more interesting don't seem to exist anymore. And part of that is the woke thing kind of came along. And I don't know what happened to those characters. But it seems not to be as much fun. And people that I talk to in that business seem to tell me the same. But I don't know.

43:08Tom Freston:That's because they're looking at streaming numbers instead of out discovering a band play. It's a different thing. I think the job has changed. But you're right. I also think that the behavior that we're talking about, sort of the lifestyle, is not rewarded in the same way that it was then. That's true.

43:24Jason Stewart:And I think that back in the day, it was like the creative people were approached by the nerdy people, the brands, the whatever, the money people. And they say, you guys are awesome. Here's a bunch of money. Do whatever you want with whatever this is. And I feel like now the nerds are drunk with power and they have the ability to call the shots. and now you know i feel like we need to get the creative people back to doing the creative work versus doing the bidding of the brands because it's the only money left yeah i mean when the money got sucked out i mean in the 90s say it was raining money for a lot of places so you could afford to make mistakes and take risks and you weren't held under such a a microscope about everything had to work and work really efficiently so it allows some sort of more creative larger than life interesting people to fit in there and survive and prosper we can't afford a mistake notice it's not raiding money anymore yeah i know you're telling me i would love to need an umbrella

44:24Tom Freston:right now um i just want to ask about mtv news because i think that if you're our age jason and i are both in our like early 40s mtv news was i mean i remember like you know life-changing events hearing about them from kurt loader gideon kurt loader tabitha soren like those people were like

44:42Jason Stewart:sort of like that's where you know they'd break in michael jackson died you put on mtv not cnn yeah

44:48Tom Freston:when kurt cobain died they break in and they they give you the news and i think that was pretty i feel like you guys did a good job of delivering that in a way that resonated with your audience but still got the the meat of the story across without having to sort of put it on training wheels yeah the people love the news and we built up a formidable news operation and uh there's a formidable news library going back to 1980 that still exists and you know mtv now become kind of a repository for uh reality shows 16 and pregnant whatever you want to you know you want to do yeah

45:21Jason Stewart:and speaking of my our condolences for your loss of ridiculousness they even saw the they saw the words music television off the bottom of the logo because they the all the music people who were there there were great people there like judy mcgrath and there's i could list a whole but they all kind of left and kind of traditional tv people came in so there's been no music equity really pumped into it the news thing got marginalized it was all about reality shows and ratings and you know so now uh there's not much of a future for running music videos on traditional cable networks the new owners there the ellisons you know they got a chance to reimagine what mtv could be as a music brand because i do believe you know people you could get some corner of the music fan audience to go for someplace where people are having intelligent conversations about music

46:13Tom Freston:i agree 100 i mean i i say i you could bring back unplugged and that would be enough honestly to some extent i think that like that concept would resonate with an older audience but also really capture a new one that hasn't experienced that before you know you can get all the you can get sabrina carpenter to do totally that you you know you can get these people that are really popular to do that stuff but i think that the opportunity feels i mean everybody still makes music videos which i always find interesting because they make more i looked it up they're making more now than ever i mean they make them more cheaply but there's still some some great ones you know no no but it's it's it's because youtube is just a music discovery survey it's like not about the video it's about a place to discover the song or the podcast right or anything thing yeah yeah it's a different thing but it's like at least the video still gets made i guess but it's surprising how many how many there are and they pump them out and but there's no context or conversation around it or even about the music so much anymore uh maybe in some places but yeah

47:09Jason Stewart:i've noticed when i go to europe they still play music videos on television so it seems like it's a the american attention span is particularly fucked i i feel like the the news and the video

47:20Tom Freston:like those two things seem very different in a lot of ways you know as far as programming goes but i i feel like was that like a struggle to make that work or did it make a lot of sense based on the audience and sort of the the way that the world felt at the time well you know when we started we used to run music videos pretty much back to back then we realized we had a bigger place if we were also about some of the things that the music was about which one of which was news and fashion and things like that so we integrated that into the programming and people were interested in that and in the beginning we found out like we did the real world which was firstly like the first reality show show changed my life tom that's one of the greatest it's real world san francisco is one of the greatest tv shows ever made young people at that age they like to look at their peers and they get a lot of signals for how they're acting and what they're doing and they're fascinated by it and uh but the problem was uh it sort of became contagious and you had celebrity reality shows we had the osborns and then the networks realized that hey these reality shows are popular and we can make them cheaper than scripted comedies or dramas so the airwaves get you know now we're into the bachelor and all these competitive shows and i don't know the apprentice would be a good example wasn't uh didn't necessarily lead to great things i mean led to success for him don't talk about omarosa like that one of our greatest

48:43Jason Stewart:One of the interesting parts about MTV's growth that I heard you mentioning in some other interviews was that it grew first, and correct me if I'm wrong, in the Midwest, in the middle of the country, and then it took some time to eventually get LA and New York on board and spread the good gospel about it. Which seems like a thing that doesn't, it's the opposite of how almost everything works. There was one simple fact for that, which was that was early days of cable. So the cable really existed really in rural areas where people needed to get distant signals in. And they had wires that allowed them to get the reception.

49:20So, you know, like a place like Tulsa or Wichita or Des Moines in the middle of America, they had large cable systems and they needed programming when the cable things started up. So we would get carried there. But no one in New York or L.A. who worked for us got us at home. There was no. you know when we launched it we had to find there was like one bar in uh new jersey that had a satellite dish there was nobody had it no one who worked there ever saw it so uh it gradually moved from the midwest what a concept moved from the midwest and you know if you were in the midwest mtv was like revolutionary in those days it wasn't a way you know hard to hard to think now you know it was uh it wasn't like a flying car or something but it had a new visual style and format that no

50:05Jason Stewart:had ever seen before might as well be an alien transmission of what's going on in the world yeah back when there was truly nothing else like that ever yeah ever those were the golden days

50:14Tom Freston:it all goes back to technology which is sort of crazy you know i always take that out of it because i don't care or don't like romanticize that but that's like kind of what it comes out to like the satellite is what kind of made it all work but cable and then the satellite i thought if if in In 1985, they had all the choices that we have today with the internet and satellite and all, you know, thousands of choices on every device. People would have loved it then. It wasn't like they suddenly got acclimated to this. It wasn't available. This is what people always wanted, to have control over what they wanted to see, wherever they wanted to see it, whenever they wanted to see it.

50:48So, you know, it's technology. You're right. Really, as it evolved, people cheered for it.

50:54Jason Stewart:Well, since we have a large brain in this space on the pod today, a lot of people talk about the reverse engineering of cable into streaming. And now there's so many streaming services. You might as well go back to cable and there's bundles and rundles and all these things going on. There's a new acquisition of a new network every day and it doesn't make any sense. How do you think the next step should be to get us back to a place that we can find some more financial success? The first thing would be to be able to tell how many streaming services they have. It's like Substack. It's like the old days of cable.

51:32There's so many of these streaming services.

51:34Tom Freston:I don't want to see your MX bill. I bet you got them all. You got Disney Plus. You got Paramount Plus. And you realize that you get Criterion in some of these niche ones, which are really good. But then you realize you don't watch them much. But it would be nice if someone could put them all together in a funnel like the old cable system. This is the new boss, same as the old boss. And then there's more choices within it. Some kind of packaging would be helpful to the consumer.

51:59Jason Stewart:Okay. I think people are working on that but using AI to potentially do that. Figure out what your tastes are based on them monitoring every single thing that you've looked at on your phone in your entire life. and they know you more than you know yourself. And then every day you open your TV or your screen or whatever, and there's 11 Criterion movies that you have never seen being recommended to you that are about to change your life and a Bravo show and a new record or whatever. Do you feel like that's good even though it's AI-based? No, I don't like that because you're in a silo and you never bump into something you don't know about.

52:41I heard someone say the other day, hey, you're on Instagram. you know when they all that stuff press on something that you don't even care about and see where that's not interesting maybe yeah yeah yeah you know shift shift your shift your

52:52Jason Stewart:algorithm and maybe okay that's what that's what the random button is for shuffle mode you know what i mean i don't have i gotta find that uh you know so you wrote this book and i feel like

53:03Tom Freston:there's been a handful of books from you know your contemporaries and in other industry you there's the Barry Diller uh there's the Graydon Carter there's the Keith McNally have you read your competition how do you think you stack up well I gotta mine's a bit different sure I mean everyone would probably say that but I mean I try to make mine more an adventure story with a business story wrapped inside and I had a different kind of career path you've done a lot of you've done a lot of fucked up shit Graydon Carter you know like Graydon Carter had some magazines yeah I mean, I took a lot of left-hand turns early on and what I found that, you know, life off the mainstream was, could be a lot more interesting.

53:40And I would pursue those things and quit jobs and do different things and go live in different countries. And what I found out was that a lot of what I picked up in those years, which was, you know, living in Asia, for example, you know, you learn about humility, you learn about empathy, you learn about being, you know, able to move, you know, with and deal with eccentric people and deal with craziness. All of it sort of prepared me for, it was a perfect fit in a way to run an enterprise like MTV Networks was in its prime, which was sort of a creative focus thing, always trying to push boundaries and dealing with a lot of young people and being tolerant.

54:18That my background was different than your traditional television executive. And it worked for me in that particular company. You know, if I was running a CBS, which really required more mainstream kind of perspective, I might not have been nearly as successful. But we attracted, you know, like in our business, I put creative people in charge of all the networks, Doug Herzog, Judy McGrath, you know, because to me, that would send a signal to the employees that creativity was our main attribute, our main aptitude. That's what we focused on. We weren't looking so much for the financial results. We were looking for creative results, wanting to encourage risk-taking and so forth.

55:00And it worked for a long time. And so I would say that if you look at my book, I mean, about two thirds of it is about stuff outside the media business.

55:12Tom Freston:I know what you mean, but I think that there's like, that was your experience, you know, with some of these, with some of these, but like some people want to write 100 pages about their childhood i don't give a fuck about that like let's get to the good stuff you had a lot of good stuff that wasn't necessarily like work related in the in the senses of the mtv sets exactly so that's a blessing that would be different for unless not to say these guys didn't have you know keith mcnally's book is great you know it's a great story about triumphing in new york with those restaurants and and barry diller and grayden i mean they were very successful but mine has more of an element of adventure to it and so i would love to drop graden in mumbai see how he does but that's a different that's a different conversation you know i took him like

55:53Jason Stewart:i took him to cuba once great and wait didn't you guys all meet fidel we all had lunch with fidel yeah i wanted to go down there just to chase down the music scene and then i told uh brian grazer about it and he said oh man i want to go but he told somebody who told somebody and the next thing I know I got a plane load of moguls flying to a communist country I knew nothing about. And when we get there, you know, it was 2001, you know, at the hotel, you know, you had the Lucky Luciano suite. That suite's all named after gangsters at the hotel. It was a crazy time in Cuba. Then they said, well, Fidel would like to meet you.

56:34Because I had made some appointments at the Ministry of Culture to try and drill into the music scene there. He said, Fidel wants to meet us. Come on. So we had lunch at the palace and he wined and dined us. And he said at one point they had us in the hall of heroes or something, the hall of ferns, which is at the presidential palace. When we met, we came, we had these rented convertibles. We came up the stairs to the palace and he's standing on the way to greet us. Fidel Castro, you know, a man from history. And I'm thinking, Jesus Christ, it's him. What's he going to say to us? And he got said, he looks at us.

57:08the first thing out of his mouth is, which one of you guys made the Sopranos?

57:11Jason Stewart:Wow. So that's what got you in the door over there. He said he's like the only subscriber of HBO in all of Cuba. And Brad Gray raises his hand. He says, that was me. So maybe they're going to shoot me, you know? I mean, Castro had a bad relationship with gangsters.

57:28Tom Freston:Guy hasn't been seen since. So at that point, going to Cuba, you just had, you have to get like a travel visa. It was like some paperwork, but you could still go. oh you had to get special visas yeah and uh you know i so i found this guy jonathan branstein from la he's a comedy manager he would go there all the time so he kind of wired me up it was just going to be me going sure before these other people came and he said you get a cultural exchange visa and i could tell you how to do it blah blah blah so this guy knew all the tricks of how to do it because it wasn't as easy as it might have been like during the obama era and then uh when it came out that we had lunch with Fidel Castro for five hours and people got a hold of that.

58:08They called the Bush White House and Cheney White House. And I got a letter saying, you went to Cuba, you had lunch with Fidel Castro, we're fining you$55 ,000.

58:17Jason Stewart:Wow. I go, whoa, whoa, man, that's, that's a ruined my day. And then, you know, we had the, I got, we got Ry Cooder. Remember Ry Cooder? He did the Buena Vista Social. Of course. He had the same problem and he got a lawyer. and I said so we got a lawyer and there's a lawyer who used to work at the treasury department fining people for doing exactly this he went to the he went to the dark side he crossed over he crossed over and now he's representing people like this so we used to prosecute so he said he get the fine down so we all hired him and you know we still have to pay a lot of money because his fees were high so you're telling me that all of you guys got hit with a fine for going yeah except Graydon Carter because uh he's Canadian he was a he was Canadian and he was a journalist oh i see they're making journalists journalists were exempt so yeah we all got hit with 55 000 fines and we had to you know hire this guy i would have sent that invoice over to the desk of fidel castro you got to pay for that one daddy but i'll call cheney and work this out i don't i can't have time for this okay that actually tom that reminds me of a question i wanted to ask you who's the last person you had dinner with where you did not pick up the check where i did not pick up the check yeah yes i had dinner last night with a guy oz wolution who's got a company called kaleidoscope he's a podcaster yeah yeah he picked up the check wow god bless him okay where'd you guys go eat i gotta look i grab as many free checks as i can i'm you know a few and far between i'm sure so you got to take them when they come well you know it's not like i'm running

59:49Tom Freston:around with an expense account anymore this is coming out of tom's pocket so you got to sort of protect the sheriff right what where do you eat in new york where where are your where are your favorite spots i live in new york by the way i i didn't i i'm just here visiting but i live i live downtown i live um right near the courthouse like sort of between chinatown and tribeca so i i'm in your general old your former area yeah well i go down there where was i the other night uh the bowery hotel in that area and i went to uh they have an la branch they just opened down there jolina oh yeah yeah yeah there's a new jolina it took a while to open it and that's good well it opened and then it had a questionable fire flood and then yeah special kind of fire kind of fire but honestly jolina in new york is a very different experience and it's pretty good and it the the room they did a really good job on the build out it's very nice like the the actual space is very nice so i like going there and you know a whole whole host of downtown spots and uptown spots i'll go to like there's a place called ilio's kind of old school italian up on the east side or the modern which is connected to moma that's kind of fun to go to if you're going to a show or something uh the i still go to the waverly over on jane street love the way over by it's on waverly yeah corner of waverly no i i hadn't been there in a long time and i went recently i forgot how fun it is it feels like a real uh relic in a good way yeah it's a nice spot yeah dark so you're in new york are you yes sir yeah yeah i've lived in new york for at this point i don't know 16 years maybe so i feel naturalized to some extent um you might agree with me but i think if new york works for you there's kind of nowhere else to live and if you like it it's kind of everything else is sort of boring yeah i i went to school here and then i just kind of always kept the place and uh after the pen you know during the pandemic a lot of people i knew they all moved out to California, Hudson Valley, Long Island, wherever, Florida.

1:01:48And a lot of them didn't come back, but I see them now starting to come back because they miss the action. I mean, I've been here all fall and it's really been fun. There's so much going on. I mean, it's hard to, you know, even we've got a new mayor coming in now. I mean, the city is sort of electric, particularly you go to South of 14th Street. You really got a good vibe that things are going on.

1:02:06Tom Freston:Yeah, up where you are, things are always the same, I think, and that's the point. It's just serene. and i at least you can come down a little bit and get the action it's not hard it's not far no do so you never lived you did you ever move the whole operation to la or were you always in new york i was new york was my base but i would spend four or six a month four to six months a year there you know because we did a lot of business there we had offices in santa monica we had a animation studio in burbank and uh i love being in la particularly in the winter particularly right around now when it's getting cold you know sure sure sure no last night yesterday I was like oh shit it's happening it's like I had to put on a real jacket yesterday exactly what I thought that cold wind comes around off the river and you go I was like I gotta put up a goddamn hat on now this is not what I bargained for I also wanted to ask you about the the vice stuff because I was very close to that and that chapter uh is funny and I think that um you captured Shane and that whole thing as a guy coming in as sort of like a successful adult I think you really captured it uh in the right way as far as like the temp check on it but i feel like you've seen a lot of fumbles in your in your career i feel like that's one of the best the worst fumbles of all time yeah they made some big fumbles and it's too bad because for a long year they had a great run you know i mean i was involved with a you know i helped get them the hbo show which really elevated their whole game and and made them better at it and they were great at it and shane was great at snipping out a cool story that was sort of on the edges and putting it together.

1:03:37He loved doing that. And in his heart, he really wanted to, you know, not just entertain, but like inform young people and take them to different corners where, you know, mainstream media wasn't covering it. And then, you know, they would spend too much on it. And, you know, there was a thing where we're always going to get bigger and bigger. We're going to grow this thing to the sky. And a lot of times the organization didn't keep up with that. But they had attracted this cadre of young journalists who really wanted to do good work there. And they did. And then, you know, because the finances were out of whack, the thing kind of imploded.

1:04:09And, you know, they bring in a private equity company and, you know, there's certain handcuffs on the business and it didn't end well.

1:04:18Tom Freston:I just know a lot of guys that I think were told very convincingly they were going to be very rich and then they aren't. It did not work out that way. options look you know you're looking at one

1:04:36Jason Stewart:you had a better bigger chunk coming for you than uh than eddie did i had a i had a chunk yeah you know that all the options were worth zero so you're saying that you but did you invest or were you just on the board i invested some money i mean was i brought in to help bring in investors uh Uh, initially then I, then they did that very well on their own. You know, they, it was a continual process, but I, I got options in the company and I helped connect them to other people. I was on the board. I was a consultant. I would spend a lot of time with them. I enjoyed going to Williamsburg and seeing it.

1:05:12And I would see Shane all around. I used to travel around. I'd see him in Afghanistan. I'd see him all over the place and his people, Ben Anderson. I knew a lot of the reporters there, Michael Moynihan. Yeah, and a lot of them who started at the very beginning had big equity positions that they were counting on. And everything was just wiped out. And then there was the investor class, the Disneys and the CVCs and all these other people who had invested to Murdoch. They all got wiped out too.

1:05:43Jason Stewart:And Shane left with how much money? You'd have to ask him.

1:05:48Tom Freston:That's how much it is, Jason. That's how much it is. I mean, he's never disclosed it. I don't know. I mean, you know, people would take out, some of these guys would take out money every year. Some of them would borrow money against their equity and like boxcars of money. And then when the thing began to implode, they had to pay it back. Jesus. Yeah, I don't like that. So it wasn't like you're not going to get anything. It's like the stuff you've got, you got to sell your houses and boats and everything. You got to pay back? Yeah, you got to sell your boat.

1:06:16Jason Stewart:god that is i mean he probably got you know at least 100 100 million what do you got that he

1:06:21Tom Freston:bought that crazy house that you met you mentioned the house like that was like a big when he did the wall street journal picture of the house people were like all right go fuck yourself this is a little mush this castle is like a bit mud um yeah well as far as investing goes have you had a real hit or have you had something that you really thought was going to go and it flopped besides vice yeah i mean i i'm kind of a conservative but i've invested in a bunch of stuff that hasn't worked sure you know but do you go outside of your interest areas or you kind of like to stay

1:06:49Jason Stewart:in stuff that wasn't there a little there's a little myspace at some point right well we looked at myspace when i was at uh when i was a ceo of viacom and uh i got promoted up to that level and uh we looked at it and we didn't ever made a bid and then rupert murdoch came in and bought it but we were interested in the social media space because we kind of saw what was coming the idea that you're going to be a gatekeeper network but now we had something where people could connect peer to peer they could come you know youtube was really to me the game changer of all you know you could upload your own video you could share it you could comment on it and all and and you know it it's now worth uh you know 550 billion dollars it's become so much more than what any of us ever imagined was possible they took that simple little model and built an infrastructure around it and kept innovating and it's like i wouldn't say it's a monster because that's a bad term i mean it's it's it's yeah it's a phenomenon it's a phenomena i think it's bigger than it ever has

1:07:53Tom Freston:been and like you said in ways that maybe people didn't expect it to be or like the use is different than people expect yeah you watch youtube tv for example that would you like what that's the greatest interface television has ever had that shit costs me 80 a month yeah it kills me yeah And now we can't get ABC. I got a Disney. I think I got a$20 Disney credit because they had a blackout recently with YouTube. I got all these emails, class action lawsuits. I don't keep up. So what is your relationship with Rupert Murdoch over the years? And how does it stand now? I haven't seen him in a while.

1:08:24I mean, we were competitors, but I was friendly with him. Of course. You know, I had issues, of course, with Fox News, but I was friendly with him. And this guy, Saad Mohseni from Afghanistan, came to see me. And he's a guy who enlisted me and invited me to come back and start this media company there after the fall of the Taliban, which I was eager to do when I left Viacom. I said, that sounds fun. I'd go back and do something kind of purposeful, and I could be back in this country that still remained a fascination to me. And then he was described to me initially as the Rupert Murdoch of Afghanistan, which, you know.

1:08:56Jason Stewart:What a title. I spit up my Pellegrino when I heard that. You're like, is that good or bad? But then he came and I said, you know what, I'm going to introduce you to the real Rupert Murdoch. And Saad had been, his father was a diplomat in Afghanistan and they were in Japan when the communist coup came. And they became refugees and they found their way to Australia. So he's Australian like Rupert. So he and Rupert really hit it off. And Rupert and News Corp became an investor in his company on successive rounds. And that was a great thing. And then, you know, he became buddies with James. And Rupert was, my ex-wife was very friendly with his wife, Wendy.

1:09:38Sure. One of his ex-wives. He's had a.

1:09:40Tom Freston:Yeah, he's had a few. Oh, Rupert's had a couple. He's had a run of them. He's had to peel off some ducats in court. But are we talking like double date friends? Are we talking like friendly when we see him at a charity event? Yeah, that. And there were times where I would double date, you know, way back. Sure, I love that. We'd never call it a double date. Hey, I'll pick you up in my car.

1:10:00Jason Stewart:Hey, Rupert Murdoch, do you want to go on a double date this weekend? No, no, I'll bring my wife.

1:10:06Tom Freston:It's not weird. We're both going to bring our wife.

1:10:09Jason Stewart:With the wives this time.

1:10:10Tom Freston:No, I think that wives will bring you together with people maybe you wouldn't, you know, maybe you'd sit across the table from in different scenarios. Look, no matter what you say about him, he's an interesting character. Totally. No, I mean, that's what I've taken away from you in general, too. And I feel like this myself. I'm attracted to the, the business is like secondary to the characters and like the personalities. Yes. That's the most interesting part of anything really. Yeah. A freak is a freak. Sometimes I think that's, what's being taken out of the business in these last few years, the personal relationship.

1:10:41Tom Freston:No, I mean, it's, that's like Jason said, like Jason said earlier, it's, it's the nerds and the numbers. And I think the personality stuff has been sort of, you know, put to the back seat and, and hopefully we can get there. You know, it doesn't seem to be trending in that direction by any means, but hopefully we can get there because I think that. bullying great again exactly first step in our initiative well maybe it's a pendulum and it swings back i hope so i think i think there's probably some there's a possibility yeah i think that that always happens to some i mean there still are there still are companies around the edges like you know look at 824 and some of these young movie studio movie companies that are pretty interesting and they still rely on gut and instinct and they take chances and uh you want to root for them but i think that i think a24 is a pretty good example and film in general is like i think that a lot of that stuff you you can miss a lot and hit a lot and it kind of evens out like you can miss a lot and hit a lot less and it evens out i guess is what i'm trying to say because i think the budgets are so the budgets vary so much depending what the project is and if it's an independent company and it isn't wedged into a public company it's not trapped into having to grow to the sky over here you know you can have a bad year but you know i'm not gonna right i'm gonna fire everybody you're still rich i'm not trying the lights off you don't have to go

1:11:53Jason Stewart:exponential hockey stick year over year until you die that's right that will ruin something all right um i guess speaking of the cyclical really quick as we end the book called unplugged obviously a reference to the mtv unplugged series maybe not a complete inspiration for it but of all uh of all the unplugs over time what has been your favorite episode oh there was a few LL Cool J. He did a great one. Wow, I got to say, that's an unexpected answer. Mamo going to knock you out. People talk about it because that was early. Playing with a band. We did an early one with Paul McCartney, the kick butt.

1:12:32Nirvana, of course, was the big one. I'll remember that so clearly. We did them with Dylan. We did them with a whole run of people. REM did a great one.

1:12:40Tom Freston:REM is my favorite.

1:12:42Jason Stewart:I'm partial to the Alice in Chains. A little more dirt under my nails than you guys. A little more working class.

1:12:47Tom Freston:well mine are painted like michael stipe so what is the what tom can we watch those any because they're not on youtube right is it on one of yeah yeah i think if you go on to paramount plus i believe they're all there there's a big library of those there's a big library of another show i really love which was on vh1 called storytellers behind the music yeah and storytellers too but behind the music is sort of the predecessor for all these music docs we see today which are also i i love them you know i'll watch almost anyone whether it's good or bad yeah i love it when

1:13:17Jason Stewart:there's a an old guy behind a mixing board and he's pulling up the old you know he's got the neve console and we're gonna bring the hi-hats in and then everyone's like oh that's that stuff that's magic yeah it doesn't even matter if it's a band i don't like i'm still watching every episode no i'm with you i'm with you and you're right they could be bringing them back now like sabrina carpenter and people like that but there's no there's no infrastructure they need to hire some music people absolutely that would be what that would be a start i think it's gonna i think

1:13:43Tom Freston:it's unfortunately going to happen probably somewhere else you know i think that that concept would be it's happening now at npr yeah i mean yeah like i said the nerds have taken over exactly yeah uh all right tom thank you for joining us uh the book is when's the book out the book comes out next uh tuesday the 18th of november next tuesday the 18th of november get

1:14:02Jason Stewart:it wherever you get books bob left sets glazing review this morning on the email he really loved that i saw left sets and that warmed my heart i was at dinner last night getting that free dinner yeah and my in by my phone started blowing up you know with all these emails about left sets and you know i read that because he's he can be harsh i mean he he cranks out so much stuff it's remarkable but he was very nice one yeah yeah we we had him a couple years ago he was a goddamn bulldog talking to him good lord he did not he did not like us he did not oh no well i think i

1:14:36Tom Freston:think he just didn't get what we were doing what is this what is this operation you're trying to run but i've been i mean i've been reading bob left sets like since 2006 like that was the first newsletter i may have ever subscribed to honestly remember it used to come out in paper yeah yeah yeah no i mean that and hits daily double where the bot that was it like that was sort of the music business news that wasn't you know from a major source but anyway all right the book is out the 18th tom thank you for joining us we appreciate it and um okay we'll see you soon Thanks Jason, thanks Chris A pleasure Tom Good talking to you guys Bye bye So, sister, have I got a little story for you?

1:15:15What you thought was your daddy was nothing but a while you were sitting home alone at age 13.

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From the publisher

Tom Freston was a co-founder of MTV who later led MTV Networks’ global expansion and served as CEO of Viacom. His great new memoir, Unplugged, is out next week. We chat with him from his home in New York about travelling overland to the Middle East in the 70s, his early ad man days, how to manage a business that's heading downhill, he has no time for audiobooks, his favorite podcasts, Trump calling up for VMA tickets back in the day, how brands took over entertainment media, our favorite Unplugged episodes, how MTV spread from middle America to LA and New York, getting fined by the American government for having lunch with Fidel Castro, when Vice was Vice, and his favorite restaurants in NY.

instagram.com/tomfrestonunplugged

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